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<h1><a href="https://archiveofourown.org/works/28719249">help to get going</a> by <a class='authorlink' href='https://archiveofourown.org/users/bunnystomped/pseuds/bunnystomped'>bunnystomped</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>the art of letting go [2]</td></tr>

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Blow Jobs, Dean Winchester Wears a Diaper, Diapers, Dry Humping, Hand Jobs, M/M</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2021-01-12</td></tr>

<tr><td><b>Updated:</b></td><td>2021-01-12</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-13 11:00:46</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,919</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/28719249</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/bunnystomped/pseuds/bunnystomped</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Cas gives him a smile, it’s small but genuine, and sets the diaper in Dean’s lap. </p><p>“Would you like help?” He asks.</p><p>“What the fuck?” Dean hisses defensively.  He can feel himself heating up with embarrassment. “I’m not a baby.”</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Series:</b></td><td>the art of letting go [2]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/2107926</td></tr>

<tr><td><b>Comments:</b></td><td>2</td></tr>

<tr><td><b>Kudos:</b></td><td>83</td></tr>

</table>

<a name="section0001"><h2>help to get going</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Just a sweet and steamy story. Dean’s beginning to become more comfortable with his love for diapers.</p><p>this is the second part of my ‘the art of<br/>letting go’ series. i didn’t realize ao3 didn’t let you post series’ anonymously. so if you saw my real account earlier no you didn’t lol</p>
    </blockquote></div><div class="userstuff module">
    
    <p>The first night was the worst for Dean. The first night after using a diaper during the day that is. He could barely sleep that night his stomach tossing and turning with feelings of guilt and shame. He shouldn't have enjoyed it as much as he did. Scratch that. He shouldn't have enjoyed it all. Despite Cas' best attempts at reassurance he still felt like a sick fuck. </p><p>He let Cas cuddle him all through the night. Let the angel rub his back and whisper sweet nothings in his ear. He loved cuddling usually. When they were at home, at the bunker, but when he was on a case he preferred to just be left alone. Well, not alone, but he didn't usually let Castiel get so close to him it fucked with his headspace. Cas understood, or at least he acted like he did for Dean's sake and always managed to keep his displays of affection to verbal gestures or extremely intense looks. He broke the unspoken rules that night though and Dean let him. Focusing on Cas' touch was better than focusing on the soggy diaper wrapped up in a plastic grocery bag in the motel trashcan. They had made it to their destination anyway he didn't need to worry about it anymore. Not until the next case that is. </p><p>And the next case did come. Somehow, Castiel managed to weasel a way into getting Sam to stay at the bunker with Jack so it would just be him and Dean. Sam gave off five flavors of confused expressions but didn't question them too thoroughly. Dean's almost certain Sam thinks that the "case" is just an excuse for Dean and Castiel to go off and have sex privately. If only it was.</p><p>There was a soft knock on Dean's door as he was packing up his duffle. Cas peaked his head inside announcing his appearance before making his way to sit beside Dean on the bed. </p><p>"Do you want to put this on before we go?" Cas asks. And yup. He's pulled out a diaper from the confines of his coat. Dean flushes red and ducks his head trying to at least act like he's searching the duffle for something. </p><p>"Dean," Cas sighs softly. He rests a hand on Dean's thigh, gives it a gentle squeeze. "You know I'm not going to judge you if you do." </p><p>"It's not you I'm worried about," Dean manages. He knows he sounds slightly breathless, but with the way his heart is pounding, he considers it a pretty steady delivery. </p><p>"Then what is?" Cas questions and he just sounds so caring it makes Dean want to melt. </p><p>"It's just not normal," Dean sighs exasperatedly. "Don't you think it's weird?"</p><p>Cas fixes him with a look that tells him he's being an utter dumbass but wraps him up in his arms nonetheless. He places gentle kisses to Dean's skin rubbing his nose along his neck. </p><p>"Dean, your entire life is abnormal," Cas tells him. "You hunt monsters for a living. You've died multiple times. Not to mention, you've entered a long term relationship with an angel of the Lord. Wearing diapers is probably the most normal thing you've ever done."</p><p>Dean snorts softly absorbing the words. Yeah, his life was pretty weird that wasn't a surprise. Maybe, putting it into perspective made it sound... Okay. He fiddles with a button on his flannel.</p><p>“Okay,” He punches the word out before he can psych himself out of agreeing. </p><p>Cas gives him a smile, it’s small but genuine, and sets the diaper in Dean’s lap. </p><p>“Would you like help?” He asks.</p><p>“What the fuck?” Dean hisses defensively.  He can feel himself heating up with embarrassment. “I’m not a baby.” </p><p>“No,” Cas agrees. “You’re not. I just know it was difficult for you last time. Dealing with the straps.” </p><p>Dean squeezes the diaper in his fingers. Yeah. It was annoying trying to get it on correctly when he was by himself. He even tried laying down to do it but even then it felt like it just wasn’t on right. He gets a little anxious about it leaking if it’s not on correctly. The padding between his fingers is soft, this diaper feels fluffier than the ones he used before. He gives it another squeeze trying to anchor himself. </p><p>“Uh. May-Maybe,” Dean begins. He makes the mistake of looking into Cas’ eyes while trying to speak and the earnest expression sends a chill down his spine. Cas just wants to help him in any way possible. “Maybe, just this time. You can help. To see how I feel?” </p><p>“Whatever pleases you Dean is what we will do,” Castiel replies stoically. </p><p>“H-how do you wanna do this?” Dean croaks, his throat dry and sticky. He bites nervously at his lower lip the diaper still clutched in his grip. </p><p>“Why don’t you undress your lower half and lay on the bed,” Castiel suggests. “I think this will be easiest.” </p><p>Dean’s hesitant to stand up and drop his drawers which is absurd as Cas has seen him naked on numerous occasions. Hell, Cas has had his dick in his mouth. He really shouldn’t be so nervous but he just can’t help it he is. He undresses with shaky hands and flops down on his back on the bed. He bends his knees and flexes his toes against the covers. </p><p>“You’ll have to relinquish the diaper, dear,” Cas jokes fondly. It’s then that Dean realizes he’s still got a death grip on the diaper. </p><p>He hands the diaper over to Cas and grips the sheets in his hands instead. </p><p>“Okay,” Cas says. “Why don’t you lift your butt up and I’ll slide the diaper right under.” </p><p>Dean does as he’s told and once the padding is under him he lets himself slowly relax down on top of it. Oh. He can’t help the gasp that escapes his lips. This diaper is definitely fluffier than the last one. His dick twitches just at the feeling of it caressing his ass. </p><p>Cas seems to notice his arousal and wraps his calloused fingers around Dean’s cock.</p><p> “Hm, you like this Dean?” Cas asks. His pupils are blown out with lust and his voice has taken on that husky tone he reserves for bedroom activities. “Having your diaper changed?”</p><p>“Fuck,” Dean moans arching his back as Cas begins to slowly jack him off. With Cas’ hand around his cock he’s decide he’s safe to be candid. “It-it’s the diaper.” </p><p>Cas hums, slowly picking up the pace, “What about it?”</p><p>Dean’s bucking into Cas’ fist quiet breathy moans escaping his lips, “It’s fluffier.”</p><p>Cas chuckles taking a moment to relish in the way Dean cries out as he teases his slit, “Yes, it’s fluffier. Thicker. More absorbent.”</p><p>“I love it,” Dean cries, his balls tensing up signalling his orgasm is nearing, and God there’s actual tears in his eyes. </p><p>“My good boy,” Cas whispers tenderly. He allows his hand to quickly jerk Dean’s cock until Dean’s toes are curling before he takes his hand away. </p><p>“Cas!” Dean shouts. “What the fuck?” </p><p>“Don’t you want to cum in your diaper?” Cas asks cheekily as he makes quick work of taping the diaper shut. He can feel shudder underneath him as the front padding makes contact with his erect penis. “Like a good boy?” </p><p>“Oh, God. Oh, God,” Dean moans. “Please. Yes, I want to cum in my diaper. I want to be good.” </p><p>“Roll over,” Cas demands and Dean complies quickly. Cas pats his padded before massaging it gently. “Hump the bed.” </p><p>“Oh, God,” Dean repeats hips already moving. He humps against the bed his dick rubbing against the soft thick padding of his diaper. The precome oozing from his slit assisting in that entrancing feeling. He’s never felt anything like this. It’s almost like fucking a girl but something about it feels so much better and that scares Dean a little. </p><p>“Cas!” Dean cries, his arm flinging out trying to find him. “Hold my hand, please. Hold my hand.” </p><p>Cas keeps one hand on Dean’s padded butt and interlocks his other hand with Dean’s. </p><p>“You’re doing so good, sweet boy,” Castiel reassures. “Humping the bed like a good boy.”</p><p>“I’m gonna cum. I’m gonna cum,” Dean chants wildly. </p><p>“Where, Dean?” Cas pushes. “Where are you gonna cum?” </p><p>“Oh, no,” Dean whines. “Cas, please.” </p><p>“C’mon sweet boy,” Cas encourages. He moves the hand on Dean’s butt a little lower massaging Dean’s balls through the diaper. “Tell me.” </p><p>“My diaper!” Dean shouts, his body growing rigid. It’s all too much. The diaper is warm and slick with precome. Cas is right there kneading his balls and holding his hand. Keeping him safe. It’s overwhelming. “I’m coming in my diaper!” </p><p>Dean’s world goes a little fuzzy for a moment. He buries his head in the bedding and lets his heart rate steady before even attempting to comprehend what just happened. He flexes his thighs together to feel that thick padding in between them. It punches another gasp out of him and makes his spent cock stir. That traitor. Cas is there. He hasn’t let go of his hand. He gives it a squeeze and Cas squeezes right back. Slowly, he comes back to himself and shakily turns onto his back. </p><p>“What the fuck was that?” Dean breathes. </p><p>“That was beautiful Dean,” Cas tells him awestruck. </p><p>Dean flushes and takes a moment to really observe Cas. The angel is flushed, his lips swollen from biting at them, and he looks so proud. </p><p>“You liked the show?” Dean teases.</p><p>“Very much” Castiel nods eagerly. </p><p>“Your turn?” Dean asks his hands already going for Cas’ fly. </p><p>“I’m sorry if I don’t last very long,” Castiel sheepishly apologizes. “You managed to get me all worked up.” </p><p>“It’s fine,” Dean snorts. “We already wasted enough time. We need to be hittin’ the road soon anyways.” </p><p>“I’m so glad you’re feeling enthusiastic,” Cas responds drily. </p><p>Cas is fully erect and dripping when Dean manages to pull him out of his pants. He’s beautiful. He squirms his body across the bed until he manages to get his lips around Cas’ cockhead. Cas never liked getting deepthroated, what he loved was having his head played with. </p><p>Dean kitten licks the slit all while maintaining eye contact with Cas. Cas liked to look in his eyes while he blew him. Dean always thought it was a little weird but it’s a lot less weird than diapers so he’s going to indulge his lover.</p><p>He wraps his fingers around Cas’ cock gently jerking him as he suckles the tip. Cas always tastes so sweet. He hums around Cas’ dick something he knows drives his boyfriend crazy. </p><p>It seems to be working. He’s bucking into Dean’s mouth more rough than usual. He really did get worked up. That makes Dean feel incredibly pleases. It was the reassurance he didn’t know he needed. Cas finds him sexy like this, diapered, so it must be okay. He hums a little louder and works his hand faster. Cas won’t last long now. </p><p>“Oh, Dean!” Cas moans his hands in Dean’s hair. “You’re s-so good.” </p><p>Cas cries out when he releases and Dean swallows it all greatly. He rests his head on Cas’ lap and smiles up at him. </p><p>“I love you,” Dean whispers like a confession. It’s not the first time he’s said it but he’s feeling especially vulnerable. </p><p>Cas leans down to kiss his lips, “I love you too, Dean.”</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>thanks for reading! comment any suggestions you have form later stories!</p></blockquote></div></div>
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